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Philadelphia Phillies: Dave Dombrowski’s history of win-now trades

George Stockburger
George Stockburger

Section 215

FT. MYERS, FL - FEBRUARY 17: Chris Sale #41 talks with Craig Kimbrel #46 of the Boston Red Sox during a team workout on February 17, 2017 at Fenway South in Fort Myers, Florida . (Photo by Billie Weiss/Boston Red Sox/Getty Images)

The Philadelphia Phillies new President of Baseball Ops has a history of pulling the trigger on big trades

In his 32 years of wheeling and dealing baseball players, Philadelphia Phillies President of Baseball Operations Dave Dombrowski has made some fairly significant trades. He’s traded away and for All-Stars and future Hall of Fame players, signaling a strong desire to win.

With Dombrowski’s hiring, we’re taking a look back at his history of big trades as a sign of what might come for the Philadelphia Phillies.

We begin with his four seasons as the general manager of the Montreal Expos, which began in 1988.

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Dombrowski’s first significant trade was not a great one on his part, but who could have foreseen a 6-10, 25-year-old becoming one of the greatest pitchers of his generation?

In1989, he traded Randy Johnson and two other players to the Seattle Mariners for All-Star pitcher Mark Langston.

Johnson would go on to win 303 games, five Cy Young awards, four ERA titles, a Triple Crown, and a World Series in 2001.

Dombrowski would also make two trades involving Gary Sheffield, first acquiring him as the general manager of the Florida Marlins and later for the Detroit Tigers.

Another future Hall of Fame player was involved in the first Sheffield deal when Dombrowski traded Trevor Hoffman and two other players to San Diego for Sheffield and reliever Rich Rodriguez.

Hoffman has cemented himself as one of the top five greatest relievers in the game’s history, recording 601 saves with a 2.87 ERA in 1,035 appearances. Like Johnson, he was a young player who didn’t have a long major league track record who was swapped for someone with proven Major League talent.

COOPERSTOWN, NY – JULY 24: Mike Piazza gives his induction speech at Clark Sports Center during the Baseball Hall of Fame induction ceremony on July 24, 2016 in Cooperstown, New York. (Photo by Jim McIsaac/Getty Images)
COOPERSTOWN, NY – JULY 24: Mike Piazza gives his induction speech at Clark Sports Center during the Baseball Hall of Fame induction ceremony on July 24, 2016 in Cooperstown, New York. (Photo by Jim McIsaac/Getty Images)

The time Dave Dombrowski acquired and traded Mike Piazza in less than 10 days.

Just five years into his career with the Los Angeles Dodgers, Piazza was already a superstar, making the All-Star game in each of his first five years and finishing as the MVP runner-up in back-to-back seasons.

After 37 games in 1998, Dombrowski traded Garry Sheffield, Bobby Bonilla, Jim Eisenreich, Manuel Barrios, and Charles Johnson to the Dodgers for Piazza and Todd Zeile, a middle-aged infielder with a career .265 batting average.

Once again, Dombrowski showed his willingness to acquire one of the game’s biggest stars while slightly mortgaging the future. Pitcher Manuel Barrios was just 23 at the time, though he never materialized into an established big league arm.

Bonilla had already signed his infamous contract with the Mets and was at the end of his career at this point. Phillies fan-favorite Jim Eisenreich was also towards the end of his career when he was traded at 39-years-old, retiring at the end of the ’98 season.

At this point, Sheffield wasn’t implicated in the Mitchell Report, which alleged he used performance-enhancing drugs. He was still an All-Star and MVP candidate when Dombrowski traded him to Los Angeles, hitting 202 home runs in 1,066 games. After the trade, he’d hit 307 home runs in 1,510 games, including the 2007-8 seasons when Dombrowski acquired him from the Yankees.

Eight days after the trade with Los Angeles, Dombrowski flipped Piazza to the New York Mets for Preston Wilson, Ed Yarnall, and Geoff Goetz.

There, Piazza continued his stellar Hall of Fame career hitting .296 with 220 home runs in eight seasons with the Mets. He’s considered one of the great catchers of his era and a legend in New York, a sign of what could have been in Florida.

DETROIT, MI – SEPTEMBER 10: Miguel Cabrera #24 of the Detroit Tigers hits a sacrifice fly ball to drive in one run against the New York Yankees during the sixth inning at Comerica Park on September 10, 2019 in Detroit, Michigan. (Photo by Duane Burleson/Getty Images)
DETROIT, MI – SEPTEMBER 10: Miguel Cabrera #24 of the Detroit Tigers hits a sacrifice fly ball to drive in one run against the New York Yankees during the sixth inning at Comerica Park on September 10, 2019 in Detroit, Michigan. (Photo by Duane Burleson/Getty Images)

Dave Dombrowski begins pulling off mega-deals with the Detroit Tigers.

Dave Dombrowski joined the Detroit Tigers front office in 2002 where he would make a game-changing trade that changed the franchise forever.

After four years of rebuilding, the Tigers made an improbably run to the World Series in 2006, ultimately losing to the St. Louis Cardinals. The team featured Ivan Rodriguez, a young Curtis Granderson, and Rookie of the Year Justin Verlander, but they needed more pieces to get over the hump.

On Dec. 5, 2007, Dombrowski pulled off a trade with his former team in Florida to acquire 24-year-old Miguel Cabrera and former Rookie of the Year Dontrelle Willis. Cabrera had reached the All-Star game in each of his first four full seasons and received MVP consideration in all five of his seasons with the Marlins.

Willis had all the potential in the world coming off a season where he was the runner-up to the Cy Young award in 2005. Despite having seven complete games that season, he followed it up with just 12 wins and a league-high 19 hit-by-pitches.

Detroit gave up the motherload of prospects, trading arguably their top two prospects Cameron Maybin and Andrew Miller in the deal. They also traded backup catcher Mike Rabelo and three minor league players to Florida in the eight-player deal.

Detroit saw themselves as contenders and somewhat mortgaged the future for a win-now opportunity. While Willis and Cabrera were young and relatively proven, though Willis went off the rails, they gave up their top two prospects and four other players.

Ultimately, neither Maybin nor Miller turned out to be the great player Cabrera proved to be, but this deal shows Dombrowski’s willingness to make the “win-now” move. Perhaps this deal is what’s motivated him in future deals, knowing that there’s a future Hall of Fame player out there who can be had for a couple of future has-beens.

DETROIT, MI – JANUARY 26: Detroit Tigers owner Mike Ilitch hands a Tigers hat to Prince Fielder while Tigers President, CEO and General Manager Dave Dombrowski looks on during the press conference to announce Fielder’s 9 year contract with the Tigers at Comerica Park on January 26, 2012 in Detroit, Michigan. (Photo by Mark Cunningham/MLB Photos via Getty Images)
DETROIT, MI – JANUARY 26: Detroit Tigers owner Mike Ilitch hands a Tigers hat to Prince Fielder while Tigers President, CEO and General Manager Dave Dombrowski looks on during the press conference to announce Fielder’s 9 year contract with the Tigers at Comerica Park on January 26, 2012 in Detroit, Michigan. (Photo by Mark Cunningham/MLB Photos via Getty Images)

Dave Dombrowski would make several franchise-altering trades for Detroit.

The Tigers largely remained in contention through the middle of Dombrowski’s tenure, reaching the ALCS in three consecutive years and losing the 2012 World Series to San Francisco. Detroit’s success hinged on the acquisition of several players during this time as Dombrowski pulled as many trades possible to keep them in contention.

On December 9, 2009, Dombrowski traded outfielder Curtis Granderson to the Yankees and Edwin Jackson to the Diamondbacks for Max Scherzer and Daniel Schlereth.

Granderson turned out to be a productive outfield bat with 344 career home runs, but once again, Dombrowski got the best of this trade. Scherzer turned into an ace in Detroit, winning his first of three Cy Young awards in 2013 with a league-high 21 wins. He’d win 82 games in Detroit before leaving in free agency, setting his legacy with the Washington Nationals by winning two more Cy Youngs and a World Series.

Dombrowski kept tinkering, trading star first baseman and recent free agent acquisition Prince Fielder to the Texas Rangers for Ian Kinsler prior to the 2014 season. Fielder had a massive contract but was limited to being a designated hitter, plus Kinsler was an above-average infielder with pop and a good glove.

That offseason Dombrowski also traded Doug Fister, acquiring future All-Star Robbie Ray and two other players.

While pushing to for a return to the Fall Classic, Dombrowski would trade prospects and young players whose names are very familiar to baseball fans today: Willy Adames, Jose Alvarez, Steve Lombardozzi, Corey Knebel, Austin Jackson, Drew Smyly, and Jake Thompson (yes, that Jake Thompson).

In return for those players, Dombrowski added shortstops Andrew Romine and Alex Gonzalez, reliever Joakim Soria, and Rays ace David Price.

The 2014 Price deal was another blockbuster that included top prospect Willy Adames in a three-team deal. Price had won a Cy Young in Tampa Bay and was ready to move into a bigger market where he could compete for a title every year. Dombrowski thought Price could bulk up the playoff rotation alongside Justin Verlander, Max Scherzer, Rick Porcello, and Anibal Sanchez, a rotation that many teams would trade the farm for today.

This deal ultimately did not work out for Detroit and set off the beginning of perpetual losing.

BOSTON, MA – JULY 05: Boston Red Sox President of Baseball Operations Dave Dombrowski talks on the phone before the game against the Texas Rangers at Fenway Park on July 5, 2016 in Boston, Massachusetts. (Photo by Adam Glanzman/Getty Images)
BOSTON, MA – JULY 05: Boston Red Sox President of Baseball Operations Dave Dombrowski talks on the phone before the game against the Texas Rangers at Fenway Park on July 5, 2016 in Boston, Massachusetts. (Photo by Adam Glanzman/Getty Images)

This is where fans get a bit weary of Dave Dombrowski.

Dave Dombrowski wants to win, and that’s what every fan should want from their front office and organization. But sometimes, winning comes at a price.

After the 2014 season, Dombrowski traded Robbie Ray and infielder Domingo Leyba to Arizona for pitcher Shane Greene. Coincidentially, Didi Gregorius was traded to the Yankees in this three-team deal.

Six days later, looking to replace Fielder’s power, the Tigers acquired Cuban outfielder Yoenis Cespedes for starting pitcher Rick Porcello. They also traded away prospect Eugenio Suárez, who hit 49 home runs for Cincinnati in 2019, for pitcher Alfredo Simón.

Following the last-ditch effort to win in 2015, it became clear that the Tigers were on the wrong track. At the trade deadline, Dombrowski sent David Price to Toronto for Daniel Norris, Matt Boyd, and Jairo Labourt. He also traded Cespedes to the Mets for pitchers Michel Fulmer and Luis Cessa, as well as Joakim Soria to Pittsburgh for JaCoby Jones.

Detroit got a solid return for those players, but Dombrowski was out of a job less than a week after the July trade deadline, released by the Tigers while four games under .500.

The Tigers really went all-in with trades for Miguel Cabrera, Ian Kinsler, David Price, Yoenis Cespedes, Shane Greene, Alfredo Simon, and Max Scherzer, but they ended Dombrowski’s run without a championship and started a lengthy rebuild.

FT. MYERS, FL – FEBRUARY 27: Craig Kimbrel #46 of the Boston Red Sox runs sprints with Chris Sale #41 before a Spring Training game against the St. Louis Cardinals on February 27, 2017 at Fenway South in Fort Myers, Florida . (Photo by Billie Weiss/Boston Red Sox/Getty Images)
FT. MYERS, FL – FEBRUARY 27: Craig Kimbrel #46 of the Boston Red Sox runs sprints with Chris Sale #41 before a Spring Training game against the St. Louis Cardinals on February 27, 2017 at Fenway South in Fort Myers, Florida . (Photo by Billie Weiss/Boston Red Sox/Getty Images)

Dombrowski blew up Boston’s farm system and won a World Series, but was it worth it?

Just days after being released from his contract in Detroit, Dombrowski joined the Boston Red Sox as President of Baseball Operations. Boston was two years removed from winning the World Series in 2014, but had finished last in the American League East the next two seasons.

Dombrowski immediately got to work and unloaded prospects Javier Guerra, Manuel Margot, Logan Allen, and Carlos Asuaje for Padres closer Craig Kimbrel. San Diego went all in after 2014 but had to reverse course, leading to them trading their All-Star closer.

Margot has shown flashes, but remains inconsistent in his time with San Diego and Tampa Bay. Logan Allen is just 23-years-old and pitched well in limited relief opportunities for Cleveland after being traded in the Trevor Bauer/Yasiel Puig deal. Asuaje appears to have been a bust and Guerra needs more opportunities, but in the immediate future, this deal largely paid off for Boston.

On December 6, 2016, the Red Sox traded two of their top prospects, 3B Yoan Moncada and RHP Michael Kopech, along with two other players for Chicago White Sox ace Chris Sale.

Moncada and Kopech were not only two of the Red Sox top prospects, but two of the best in baseball. It was another clear win-now move for Dombrowski to acquire a top of the rotation starter to pair with former Tigers Rick Porcello, Doug Fister, and David Price.

In the short-term, these moves paid off big for the Red Sox, who won another World Series in 2018 on the arms of Kimbrel and Sale. While winning a World Series is the ultimate goal, Boston unloaded their farm system and is facing a lengthy rebuild, similar to Detroit’s.

This trend with Dombrowski is the biggest fear among Philadelphia Phillies fans; he’ll go all-in to win this year and sell the farm in the process, only to leave the franchise in a smoldering mess for the next decade.

Does this mean Dombrowski will do the same with in Philadelphia by trading Alec Bohm for a 32-year-old pitcher? In that case, probably not. One thing preventing Dombrowski from selling the farm to win now is the fact that the Philadelphia Phillies farm system is completely bare. Other than recent first-round picks Bryson Stott and Mick Abel, Philly’s farm system needs several years’ worth of solid drafts to get back to where it was in 2006.

Dombrowski’s attention for rebuilding the Philadelphia Phillies in the immediate future should be in free agency with J.T. Realmuto and Didi Gregorius. The big trades will come, but right now he doesn’t have the ammo to do it.

Honorable Mention Trades

On July 5, 2002, Dombrowski acquires future All-Star Carlos Pena in a three-team deal with the Oakland A’s and New York Yankees. The deal was later featured in the movie Moneyball.

On July 31, 2006,  Dombrowski acquired All-Star first baseman Sean Casey for minor-league pitcher Brian Rogers.

On July 23, 2012, Dombrowski traded former first round pitcher Jacob Turner, catcher Rob Brantly, and pitcher Brian Flynn to the Miami Marlins for starting pitcher Aníbal Sánchez and infielder Omar Infante.

George Stockburger

George Stockburger

Graduate of Penn State University, Executive Digital Producer for WETM 18 News, Former Editor for NFL Mocks and That Ball's Outta Here